Isopropanol → 1-Methyl-4-(2-thiophen-3-yl-pyridin-4-yl)-piperazine

HRID 910673Notes

Reaction equation

HRID 910673 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:3]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CC(O)C>Cl.O>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3[CH:12]=[CH:11][S:10][CH:9]=3)[CH:3]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 531671-MethylpiperazineHCID 672422234-Chloro-2-thiophen-3-yl-Pyridine

Product 1

HCID 252181461-Methyl-4-(2-thiophen-3-yl-pyridin-4-yl)-piperazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

To a microwave tube was added 4-chloro-2-thiophen-3-yl-pyridine (50 mg, 0.26 mmol), 1-methylpiperazine (100 mg, 1 mmol), 2-propanol (0.7 mL) and concentrated HCl (1 drop). The resulting mixture was heated at 180° C. for 40 min using a Personal Chemistry Smith Synthesizer. The resulting mixture was poured into water and extracted with CH2Cl2. The organic layer was dried and concentrated, and the residue was purified by preparative TLC (CH2Cl2/MeOH) to yield the title compound as a solid.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by preparative TLC (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-4e34362b413945fd84f4b7e02aae39dc
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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